Joseph: This is another great synthesis, Write up a brief description, and I think you have this one nailed as well. Bruce Bondurant JOSEPH WILLIAMS
THIS SYNTHESIS IS DESCRIBES HOW MEPARFYNOL IF MADE FRON SCATCH USING TRIPLE BONDED CARDON SHORT CHAINS. IN THE REACTION WE USE SODIUM AMINE IN THE PRESENCE OF THE H2C2 TO PROTONATE THE H ATOM AND MAKE A H3C2 AND 1-BUTYNE. THIS REPRESENT THE FIRLST REACTION THAT TAKES PLACE IN THE SYNTHESIS OF MARPAFYNOL. WE ALSO ADD HGSO4 ADN H2SO4 TO MAKE AND ALCOHOL AND A KETONE OUT OF IT.
THE THIRD REACTION INCLUDES THE ADDTION OF NANH2 TO MAKE AN ACYTALIDE ION AS DISCUSSED IN CLASS B DR BONDURANT AND WE DO THIS IN THE PRESENCE OF TOULENE IF AVAILABLE.
THE NA ION THEN REACTS WITH THE H2C2 . THE FINAL PRODUCT OF THEN MARPAFYNOL.
Literature References: Prepd from methyl ethyl ketone and sodium acetylide in liquid ammonia or by a Grignard reaction: DE285770 (1913 to Bayer); also DE289800 and DE291185seeFrdl.12, 55, 56, 57; Sung Wouseng, Ann. Chim. [10] 1, 343 (1924); Rupe, Vonaesch, Ann.442, 80 (1925); Carothers, Coffman, J. Am. Chem. Soc.54, 4071 (1932); Campbell et al.,ibid.60, 2882 (1938); Campbell, Campbell, Proc. Indiana Acad.
Percent Composition: C 59.56%, H 7.85%, N 9.92%, O 22.67%
Literature References: Prepn: McLamore et al.,J. Org. Chem.20, 1379 (1955); from 3-methyl-1-pentyn-3-ol, trichloroacetic acid, KOCN: McCrea et al.,GB761817 (1956 to British Schering). Acute toxicity: Soehring et al.,Arzneim.-Forsch.5, 161 (1955).
Properties: Crystals from ether + petr ether. mp 55.8-57° (McLamore); from cyclohexane, mp 53.5-55° (McCrea). bp16 120-121°; bp0.01 95°. Solubility in water: 1.6 g/100 ml. LD50 (4 hr) s.c. in mice: 0.56 g/kg (Soehring).
THIS SYNTHESIS IS ALSO RFLECTED IN WADES ORGANIC CHEMISTRY BOOK CHANPTER 10 AND FROM ORGANIC CHEMISTRY. COM,/ JOSEPH WILLIAMS ( EXTRA CREDIT)
Sandra Zivkovic Resources: Winter, Arthur. Organic Chemistry I for Dummies. Indianapolis: Wiley. Hathaway, Bruce A.Organic Chemistry: The Easy Way//. Hauppauge: Barron's Educational Series, 2005. Wade: Mechanism chapters and notes from class
Joseph: This is another great synthesis, Write up a brief description, and I think you have this one nailed as well.
Bruce Bondurant
THIS SYNTHESIS IS DESCRIBES HOW MEPARFYNOL IF MADE FRON SCATCH USING TRIPLE BONDED CARDON SHORT CHAINS. IN THE REACTION WE USE SODIUM AMINE IN THE PRESENCE OF THE H2C2 TO PROTONATE THE H ATOM AND MAKE A H3C2 AND 1-BUTYNE. THIS REPRESENT THE FIRLST REACTION THAT TAKES PLACE IN THE SYNTHESIS OF MARPAFYNOL. WE ALSO ADD HGSO4 ADN H2SO4 TO MAKE AND ALCOHOL AND A KETONE OUT OF IT.
THE THIRD REACTION INCLUDES THE ADDTION OF NANH2 TO MAKE AN ACYTALIDE ION AS DISCUSSED IN CLASS B DR BONDURANT AND WE DO THIS IN THE PRESENCE OF TOULENE IF AVAILABLE.
THE NA ION THEN REACTS WITH THE H2C2 . THE FINAL PRODUCT OF THEN MARPAFYNOL.
Title: Meparfynol
CAS Registry Number: 77-75-8
CAS Name: 3-Methyl-1-pentyn-3-ol
Additional Names: ethyl ethynyl methyl carbinol; 2-ethynyl-2-butanol; methylparafynol; methylpentynol
Trademarks: Allotropal (Heyl); Anti-Stress (Sintyal); Apridol; Atemorin; Atempol (Norgine); Dalgol; Dorison; Dormalest; Dormidin; Dormigen; Dormiphen; Dormison (Schering); Dormosan; Formison; Hesofen; Hexofen; Imnudorm; Oblivon; Pentadorm; Perlopal; Riposon; Seral; Somnesin (Central Pharm.)
Molecular Formula: C6H10O
Molecular Weight: 98.14
Percent Composition: C 73.43%, H 10.27%, O 16.30%
Literature References: Prepd from methyl ethyl ketone and sodium acetylide in liquid ammonia or by a Grignard reaction: DE 285770 (1913 to Bayer); also DE 289800 and DE 291185 see Frdl. 12, 55, 56, 57; Sung Wouseng, Ann. Chim. [10] 1, 343 (1924); Rupe, Vonaesch, Ann. 442, 80 (1925); Carothers, Coffman, J. Am. Chem. Soc. 54, 4071 (1932); Campbell et al., ibid. 60, 2882 (1938); Campbell, Campbell, Proc. Indiana Acad.
Melting point: mp -30.6°
Boiling point: bp760 121-122°; bp37 50°; bp6.5 20°
Flash point: Flash pt 101.3°F
Index of refraction: nD20 1.4318
Density: d420 0.8688; d2020 0.8721; 7.28 lbs/U.S. gal
Toxicity data: LD50 orally in mice, rats, guinea pigs: 600-900 mg/kg (Margolin)
Derivative Type: Carbamate
CAS Registry Number: 302-66-9
Trademarks: N-Oblivon; Oblivon C; Trusono
Molecular Formula: C7H11NO2
Molecular Weight: 141.17
Percent Composition: C 59.56%, H 7.85%, N 9.92%, O 22.67%
Literature References: Prepn: McLamore et al., J. Org. Chem. 20, 1379 (1955); from 3-methyl-1-pentyn-3-ol, trichloroacetic acid, KOCN: McCrea et al., GB 761817 (1956 to British Schering). Acute toxicity: Soehring et al., Arzneim.-Forsch. 5, 161 (1955).
Properties: Crystals from ether + petr ether. mp 55.8-57° (McLamore); from cyclohexane, mp 53.5-55° (McCrea). bp16 120-121°; bp0.01 95°. Solubility in water: 1.6 g/100 ml. LD50 (4 hr) s.c. in mice: 0.56 g/kg (Soehring).
Melting point: mp 55.8-57° (McLamore); mp 53.5-55° (McCrea)
Boiling point: bp16 120-121°; bp0.01 95°
Toxicity data: LD50 (4 hr) s.c. in mice: 0.56 g/kg (Soehring)
Therap-Cat: Hypnotic; sedative.
THIS SYNTHESIS IS ALSO RFLECTED IN WADES ORGANIC CHEMISTRY BOOK CHANPTER 10 AND FROM ORGANIC CHEMISTRY. COM,/ JOSEPH WILLIAMS ( EXTRA CREDIT)
Sandra Zivkovic
Resources: Winter, Arthur. Organic Chemistry I for Dummies. Indianapolis: Wiley. Hathaway, Bruce A. Organic Chemistry: The Easy Way//. Hauppauge: Barron's Educational Series, 2005. Wade: Mechanism chapters and notes from class